CNN  — 

If Gregory Cheadle had not cracked a joke, his life would be a lot less complicated today.

His troubles began when he attended a rally by then-presidential candidate Donald Trump in Redding, California, in June 2016. Cheadle was a California congressional candidate at the time, and he stood out as a Black Republican.

As Cheadle watched from the VIP section of the overwhelmingly white crowd, Trump went into an extended riff about a Black supporter who had assaulted an anti-Trump protester at an Arizona rally. Trump wondered aloud where his supporter was when Cheadle decided to play along and shouted, “I’m here!”

“Oh, look at my African American over here,” Trump responded with a smile, pointing at Cheadle as some people in the crowd cheered. “Look at him. Are you the greatest?”

Cheadle laughed along with everyone else, but that soon changed. He left the rally early, took a nap at a friend’s house, and by the time he woke up, he had gone viral.

His phone was filled with texts and voicemails from reporters wanting interviews. There also were angry messages from family and friends wanting to know why he let Trump insult him. His Facebook page was filled with both Black and White people calling him “Uncle Tom” and the N-word and threatening to kick his butt.

“Oh, you got to be kidding,” he thought at the time. “America doesn’t have anything better to do than this?”

Cheadle was about to discover the loneliest place in the universe may be reserved for a man who becomes known as Trump’s Black buddy.

“Man, I did it for a joke,” he says now. “When I did it, people around me burst out laughing.” He sighs before adding: “Then the joke turned sour.”

How Cheadle’s life changed

President Donald Trump’s “great relationship with the Blacks” is back in the news. As the 2020 presidential race heads into the home stretch, one of its biggest storylines has been Trump’s vigorous attempt to recruit more Black support. Many of the top speaking slots at last month’s Republican National Convention were reserved for Black speakers.

The Trump campaign has also purchased ads in local Black radio stations and newspapers. In what may be another close election, Trump’s ability to pick off more Black voters could make the difference between winning and losing. Some polls suggest that Trump is actually performing better with Black voters than he did four years ago.

President Donald Trump shakes hands with Republican Sen. Tim Scott of South Carolina at the White House in February 2018. Scott was one of several prominent Black speakers at the Republican National Convention last month.

What’s happened to Cheadle since that day in 2016, though, shows how tough the Trump campaign’s challenge is going to be. For starters, he is no longer Trump’s “African American friend.”

Cheadle, 63, a real estate broker and a volunteer at a hospital emergency room, says he is a very different man than the one who went to hear Trump four years ago. He’s lost friends and gone into hiding. Trump’s shout-out even shook up his love life.

“I was dating a woman and we broke up because of that,” he says. “The whole thing was kind of stupid. She was an influential Democrat and she just couldn’t handle the pressure of even being seen in public with someone associated with Trump.”

Cheadle says he has since lost respect for some Black Republican conservatives. He compares them to ventriloquists’ dolls – puppets employed by powerful white people to mouth political platitudes that hurt Black people.

He also says he was deflated by how the Republican party reacted to the death of Herman Cain, a former Republican presidential candidate. Cain, who was Black, died after contracting coronavirus soon after attending a Trump rally without wearing a mask.

“It was sad that he died, but even more sad that he was not given any honor by the Republican Party,” Cheadle says. “It was like, ‘He’s dead. No problem. Goodbye.’”

Former 2012 Republican presidential candidate Herman Cain at a Trump rally on June 20 in Tulsa, Oklahoma. Cain died of Covid-19 in July.

Only 8% of Black Americans voted for Trump in 2016. Cheadle doesn’t think Trump will pick up more Black support in November.

“I would be surprised if he did as well (with Black voters) as he did last time,” he says.

Yet polls show that about 10% of Black voters still support Trump today. Ravi Perry, a political scientist, is not surprised by that number. Ever since the mid-1960s, when he says the Republican Party adopted an anti-civil rights agenda, about 10% of Black voters have supported the GOP.

“Even when Obama was on the ticket, he got like 95% of the Black vote,” says Perry, chairman of the political science department at Howard University in Washington. He says some Black Republicans have long put more emphasis on conservative principles than skin color. They like Trump’s record of appointing conservative federal judges, for example.

But Perry is not optimistic about Trump’s chances of plucking off more Black voters in November because of how Trump is perceived. One recent poll found that more than 8 in 10 Black voters think the President is a racist.

“I don’t think there’s much they can do (to sway voters),” Perry says of Trump’s Black campaign surrogates. “All they can do between now and November is ignore the racial elements of the Trump administration.”

Why he soured on Trump

Cheadle won’t play along with that strategy. The divorced father of three is a gregarious man whose voice rises when he starts talking about Trump’s treatment of Blacks. He grew up in inner-city Oakland and Cleveland and still remembers seeing race riots erupt during the mid-1960s.

He is not an unusual character in the Black community. Virtually every major Black leader – Frederick Douglass, Booker T. Washington, Malcolm X and even Obama – has blended conservative principles like self-help and economic empowerment with progressive ideas.

But Cheadle remains skeptical about the Democratic Party. He doesn’t like Obamacare and didn’t vote for Obama because he says Obama was an “elitist” who never did much for Black people. He doesn’t think Joe Biden, the Democratic presidential nominee, has done much for Black people, either.

And Cheadle still reveres the Republican Party, or at least the 19th-century version of it, which was willing to go to war to end slavery.

“They freed the slaves,” he says of the party of Lincoln. “They literally gave their lives for the cause.”

That’s part of the history Cheadle carried with him when he went to hear Trump speak in 2016. He thought the media portrayals of Trump were too harsh, and he wanted to have an open mind.

Many thought that Trump’s comment that day – “my African-American” – was condescending. Cheadle didn’t think so at the time.

Trump, speaking at that June 2016 rally, has struggled to win over Black voters.

“We’re so polarized and sensitive in this country now. It’s frightening,” he said a day after the rally.

Some of the attention Cheadle received after that 2016 rally was positive. He appeared on CNN and PBS, and Stephen Colbert’s show featured him in a segment. He started getting recognized more when he went out in public to campaign for his congressional seat.

But as the threats and verbal abuse continued to pour in, he started thinking of what happened to Gabrielle Giffords, the former congresswoman from Arizona, who was wounded by a gunman in 2011 at a political event.

“I pretty much went into hiding,” Cheadle says. “I didn’t want to really be in public because it was too ugly. This is gun country up here. People don’t play.”

Cheadle ending up moving from Northern California to Southern California after he lost his congressional bid. He then made another move. He left the Republican Party last year because of what he describes as its “pro-white agenda” and Trump’s inflammatory racial rhetoric.

Cheadle says he was bothered by Trump’s comments last year when he told four congresswomen of color to “go back” to where they came from. He also didn’t like the fact that the overwhelming majority of Trump’s cabinet and judicial appointments went to white men. “When you look at the White House, it really is a white house,” he says.

But he refuses to call Trump a racist because the term is so loaded. Instead he says Trump has a “white superiority complex.”

“When you say someone is racist, it’s damning but it’s not productive,” he says.

How he’s voting in 2020

The George Floyd racial protests and the resurgence of Black Lives Matter also hit Cheadle deeply. He says the Floyd video made “me sick to my stomach.”

And his politics have evolved so much in recent years that he no longer calls himself a conservative.

“A conservative means you’re in favor of the status quo, and the status quo is keeping the white superiority complex in power,” he says. “I’m not for that. I am an independent, an independent thinking person.”

But he hasn’t made another big decision – who he’s going to vote for in November. He calls himself undecided between Biden and Trump.

gregory cheadle trump my african american ctn intv
Man Trump called 'my African-American' leaves GOP
01:52 - Source: CNN

“You’re asking me to choose between projectile vomit and diarrhea,” he says.

Cheadle does like Biden’s vice-presidential pick, Kamala Harris. She would be the first vice-president who is Black and South Asian. He believes Harris’ race could make her more empathetic toward Black people.

“If I vote for Biden, it’ll probably be because I’m voting for Harris,” he says.

And Cheadle hasn’t given up on politics. He plans on running for office again.

Does he ever worry that he’ll forever be known as Trump’s “African American?” Just last month, a news crew from India contacted him seeking an interview about his famous exchange with Trump.

“It doesn’t worry me,” he says. “In the overall scheme of things, I’m happy that it happened. It’s given me a platform to use to better my people. All of that headache and the names I’ve been called is a small price to pay.”

Trump has since found new Black allies, including former NFL running back Herschel Walker, who recently said “it hurt my soul” to hear people call Trump a racist.

We’ll find out in November if these Black supporters make any difference.

In the meantime, Cheadle has finally got enough distance from that Trump rally in 2016 to start working on his memoir. He already has a title.

It’s called, “My African American.”